WO2003082244A2 - Hfa-suspensionsformulierungen eines anhydrats - Google Patents
Hfa-suspensionsformulierungen eines anhydrats Download PDFInfo
- Publication number
- WO2003082244A2 WO2003082244A2 PCT/EP2003/002899 EP0302899W WO03082244A2 WO 2003082244 A2 WO2003082244 A2 WO 2003082244A2 EP 0302899 W EP0302899 W EP 0302899W WO 03082244 A2 WO03082244 A2 WO 03082244A2
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- hfa
- acid
- contain
- suspensions
- tiotropium
- Prior art date
Links
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/0012—Galenical forms characterised by the site of application
- A61K9/007—Pulmonary tract; Aromatherapy
- A61K9/0073—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy
- A61K9/008—Sprays or powders for inhalation; Aerolised or nebulised preparations generated by other means than thermal energy comprising drug dissolved or suspended in liquid propellant for inhalation via a pressurized metered dose inhaler [MDI]
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/439—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom the ring forming part of a bridged ring system, e.g. quinuclidine
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K9/00—Medicinal preparations characterised by special physical form
- A61K9/10—Dispersions; Emulsions
- A61K9/12—Aerosols; Foams
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
Definitions
- the invention relates to propellant gas preparations for metered dose aerosols with suspension formulations of the crystalline anhydrate of (1c., 2ß, 4ß, 5 ⁇ , 7ß) -7- [(hydroxydi-2-thienylacetyl) oxy] -9,9-dimethyl-3-oxa-9- azoniatricyclo [3.3.1.0 2 ' 4 ] nonane bromide.
- Patent application EP 418 716 A1 known and has the following chemical
- Tiotropium bromide is preferably administered by inhalation.
- the object of the present invention is to provide HFA metered dose aerosols containing tiotropium bromide as the only active substance in suspended form.
- the present invention relates to suspensions of this crystalline tiotropium bromide anhydrate in the propellant gases HFA 227 and / or HFA 134a, optionally in a mixture with one or more further propellant gases, preferably selected from the group consisting of propane, butane, pentane, dimethyl ether, CHCIF 2 , CH 2 F 2) CF 3 CH 3 , isobutane, isopentane and neopentane.
- crystalline tiotropium bromide anhydrate in the context of the present invention, this should be regarded as a reference to the anhydrous, crystalline modification of the tiotropium bromide which can be obtained by drying the crystalline tiotropium bromide monohydrate.
- this crystal modification is optionally also referred to as crystalline tiotropium bromide in anhydrous form.
- suspensions are preferred according to the invention which contain only HFA 227, a mixture of HFA 227 and HFA 134a or only HFA 134a as the propellant gas. If a mixture of the propellant gases HFA 227 and HFA 134a is used in the suspension formulations according to the invention, the weight ratios in which these two propellant gas components can be used are freely variable.
- one or more further propellants are selected in the suspension formulations according to the invention, selected from the group consisting of propane, butane, pentane, dimethyl ether, CHCIF 2 , CH 2 F 2 , CF 3 CH 3 , isobutane, If isopentane and neopentane are used, the proportion of this further propellant gas component is preferably below 50%, preferably below 40%, particularly preferably below 30%.
- the suspensions according to the invention preferably contain between 0.001 to 0.8% tiotropium. Suspensions which contain 0.08 to 0.5%, particularly preferably 0.2 to 0.4% tiotropium are preferred according to the invention.
- Tiotropium is the free ammonium cation.
- the propellant gas suspensions according to the invention are characterized in that they contain tiotropium in the form of the crystalline tiotropium bromide anhydrate which is outstandingly suitable for this application. Accordingly, the present invention preferably relates to suspensions containing between 0.0012 and 96% crystalline tiotropium bromide anhydrate. Of particular interest according to the invention are suspensions which contain 0.096 to 0.6%, particularly preferably 0.24 to 0.48%, crystalline tiotropium bromide anhydrate.
- the percentages given in the context of the present invention are always mass percentages. If mass fractions for tiotropium are expressed in mass percentages, the corresponding values for the crystalline tiotropium bromide anhydrate preferably used in the context of the present invention can be obtained by multiplying by the conversion factor 1, 2036.
- suspension formulation may also be used instead of the term suspension. Both terms are to be regarded as equivalent within the scope of the present invention.
- the inhalation aerosols or suspension formulations containing propellant gas according to the invention may also contain further constituents such as surface-active agents (surfactants, surfactants), adjuvants, antioxidants or flavoring agents.
- surface-active agents surfactants, surfactants, adjuvants, antioxidants or flavoring agents.
- the surface-active agents (surfactants, surfactants) optionally contained in the suspensions according to the invention are preferably selected from the group consisting of polysorbate 20, polysorbate 80, Myvacet 9-45, Myvacet 9-08, isopropyl myristate, oleic acid, propylene glycol, polyethylene glycol, Brij, ethyl oleate, Glyceryl trioleate glyceryl monolaurate, glyceryl monooleate, glyceryl monosterate, glyceryl monoricinoleate, cetyl alcohol, steryl alcohol, cetyl pyridinum chloride, block polymers, natural oil, ethanol and isopropanol.
- polysorbate 20, polysorbate 80, Myvacet 9-45, Myvacet 9-08 or isopropyl myristate are preferably used.
- Myvacet 9-45 or isopropyl myristate are particularly preferably used.
- surface-active agents are present in the suspensions according to the invention, these are preferably used in a proportion of 0.0005-1%, particularly preferably 0.005-0.5%.
- the adjuvants optionally contained in the suspensions according to the invention are preferably selected from the group consisting of alanine, albumin, ascorbic acid, aspartame, betaine, cysteine, phosphoric acid, nitric acid, hydrochloric acid, sulfuric acid and citric acid.
- Ascorbic acid, phosphoric acid, hydrochloric acid or citric acid are particularly preferably used, particularly preferably hydrochloric acid or citric acid. If adjuvants are present in the suspensions according to the invention, these are preferably used in a proportion of 0.0001-1.0%, preferably 0.0005-0.1%, particularly preferably 0.001-0.01%, a proportion of 0.001 -0.005% according to the invention is of particular importance.
- the antioxidants optionally present in the suspensions according to the invention are preferably selected from the group consisting of ascorbic acid, citric acid, sodium edetate, editic acid tocopherols, butylated hydroxytoluene, butylated hydroxyanisole and ascorbyl palmitate, with tocopherols, butylated hydroxytoluene, butylated hydroxyanisole or ascorbyl palmitate being used with preference.
- the flavoring agents optionally contained in the suspensions according to the invention are preferably selected from the group consisting of peppermint, sacharin, dentomint, aspartame and essential oils (for example cinnamon, anise, menthol, camphor), with peppermint or Dentomint® being particularly preferred.
- Process obtained in finely divided form.
- the active substance After micronization, the active substance preferably has an average particle size of 0.5 to 10 ⁇ m, preferably 1 to 6 ⁇ m, particularly preferably 1.5 to 5 ⁇ m. At least 50%, preferably at least 60%, particularly preferably at least 70% of the active ingredient particles preferably have a particle size which lies within the size ranges mentioned above. Particularly preferred at least 80%, most preferably at least 90% of the active ingredient particles with their particle size are in the ranges mentioned above.
- suspensions can also be prepared which, in addition to the propellant gases mentioned, only contain the active ingredient and no further additives. Accordingly, a further aspect of the present invention is aimed at suspensions which only contain the active ingredient without further additives.
- the suspensions according to the invention can be prepared by methods known in the art.
- the constituents of the formulation are mixed with the propellant gas (s) (if appropriate at low temperatures) and filled into suitable containers.
- pMDIs pressurized metered dose inhalers
- a further aspect of the present invention relates to medicaments in the form of suspensions as described above in connection with one or more inhalers suitable for the administration of these suspensions.
- the present invention relates to inhalers, characterized in that they contain suspensions containing propellant gas according to the invention described above.
- the present invention further relates to containers (cartridges) which can be used with a suitable valve in a suitable inhaler and which contain one of the above-mentioned suspensions containing propellant gas according to the invention. Suitable containers (cartridges) and methods for filling these cartridges with the suspensions containing propellant gas according to the invention are known from the prior art.
- the present invention further relates to the use of the suspensions according to the invention for the manufacture of a medicament which can be administered by inhalation or nasal administration, preferably for the manufacture of a medicament for the inhalative or nasal treatment of diseases in which anticholinergics can have a therapeutic benefit.
- the present invention particularly preferably further relates to the use of the suspensions according to the invention for producing a medicament for inhalation treatment of respiratory diseases, preferably asthma or COPD.
- the tiotropium bromide obtainable according to EP 418 716 A1 can be used to prepare the crystalline tiotropium bromide monohydrate. This is then implemented as described below.
- the crystalline tiotropium bromide monohydrate obtainable according to the procedure described above was subjected to an investigation by means of DSC (differential scanning calorimetry).
- the DSC diagram has two characteristic signals. The first, relatively broad, endothermic signal between 50-120 ° C is due to the dehydration of the tiotropium bomide monohydrate to the anhydrous form. The second, relatively sharp, endothermic maximum at 230 ⁇ 5 ° C is attributable to the melting of the substance.
- This data was obtained using a Mettler DSC 821 and evaluated using the Mettler software package STAR. The data were collected at a heating rate of 10 K / min.
- the crystalline tiotropium bromide monohydrate was characterized by means of IR spectroscopy. The data were collected using a Nicolet FTIR spectrometer and evaluated with the Nicolet software package OMNIC, version 3.1. The measurement was carried out with 2.5 ⁇ mol tiotropium bromide monohydrate in 300 mg KBr.
- AFC7R-4 circular diffractometer Rasterku
- the structure solution and refinement of the crystal structure was carried out using direct methods (program SHELXS86) and FMLQ refinement (program TeXsan).
- the crystalline tiotropium bromide monohydrate obtained as described above is dried by careful drying at 80-100 ° C. under reduced pressure, preferably in a high vacuum for a period of at least 30
- the anhydrous form can also be produced by storing it over dried silica gel at room temperature for a period of at least 24 hours.
- the crystalline tiotropium bromide anhydrate obtainable by the above process is micronized according to processes known per se in the prior art with the exclusion of moisture in order to provide the active ingredient in the form of the average particle size which corresponds to the specifications according to the invention.
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Dispersion Chemistry (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Otolaryngology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Medicinal Preparation (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims
Priority Applications (16)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CA2479638A CA2479638C (en) | 2002-03-28 | 2003-03-20 | Hfa-suspension formulations of crystalline tiotropium bromide anhydrate |
MEP-2008-473A ME00246B (de) | 2002-03-28 | 2003-03-20 | Hfa-suspensionsformulierungen eines anhydrats |
EA200401159A EA008610B1 (ru) | 2002-03-28 | 2003-03-20 | Суспензионные препараты на основе кристаллического ангидрата тиотропийбромида |
JP2003579782A JP5147158B2 (ja) | 2002-03-28 | 2003-03-20 | 無水物のhfa懸濁製剤 |
YU86004A RS52481B (en) | 2002-03-28 | 2003-03-20 | FORMULATION OF HFA-SUSPENSION CONTAINING ANHYDRATE |
MXPA04009338A MXPA04009338A (es) | 2002-03-28 | 2003-03-20 | Formulaciones de un anhidrato en suspension con hfa. |
UA20041008758A UA79776C2 (en) | 2002-03-28 | 2003-03-20 | Hfa-suspension formulation of crystalline tiotropium bromide anhydrate and use thereof |
IL16369603A IL163696A0 (en) | 2002-03-28 | 2003-03-20 | Hfa-suspension formulation of an anhydrate |
KR1020047015174A KR101005717B1 (ko) | 2002-03-28 | 2003-03-20 | 무수물의 hfa-현탁 제형 |
EP03717219A EP1492498A2 (de) | 2002-03-28 | 2003-03-20 | Hfa-suspensionsformulierungen eines anhydrats |
NZ536030A NZ536030A (en) | 2002-03-28 | 2003-03-20 | HFA-suspension formulation of crystalline tiotropium bromide anhydrate |
BR0308709-3A BR0308709A (pt) | 2002-03-28 | 2003-03-20 | Formulações em suspensão de hfa de um anidrato |
AU2003221509A AU2003221509B2 (en) | 2002-03-28 | 2003-03-20 | HFA-suspension formulation of an anhydrate |
ZA2004/05637A ZA200405637B (en) | 2002-03-28 | 2004-07-15 | Hfa-suspension formulation of an anhydrate |
NO20044004A NO20044004L (no) | 2002-03-28 | 2004-09-23 | HFA-Suspensjonsformulering av et anhydrat |
HR20040890A HRP20040890A2 (en) | 2002-03-28 | 2004-09-27 | Hfa-suspension formulation of an anhydrate |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10214264.5 | 2002-03-28 | ||
DE10214264A DE10214264A1 (de) | 2002-03-28 | 2002-03-28 | HFA-Suspensionsformulierungen eines Anhydrats |
Publications (2)
Publication Number | Publication Date |
---|---|
WO2003082244A2 true WO2003082244A2 (de) | 2003-10-09 |
WO2003082244A3 WO2003082244A3 (de) | 2004-02-05 |
Family
ID=28050990
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2003/002899 WO2003082244A2 (de) | 2002-03-28 | 2003-03-20 | Hfa-suspensionsformulierungen eines anhydrats |
Country Status (21)
Country | Link |
---|---|
EP (1) | EP1492498A2 (de) |
JP (1) | JP5147158B2 (de) |
KR (1) | KR101005717B1 (de) |
CN (1) | CN1642525A (de) |
AU (1) | AU2003221509B2 (de) |
BR (1) | BR0308709A (de) |
CA (1) | CA2479638C (de) |
DE (1) | DE10214264A1 (de) |
EA (1) | EA008610B1 (de) |
EC (1) | ECSP045322A (de) |
HR (1) | HRP20040890A2 (de) |
IL (1) | IL163696A0 (de) |
ME (1) | ME00246B (de) |
MX (1) | MXPA04009338A (de) |
NO (1) | NO20044004L (de) |
NZ (1) | NZ536030A (de) |
PL (1) | PL371295A1 (de) |
RS (1) | RS52481B (de) |
UA (1) | UA79776C2 (de) |
WO (1) | WO2003082244A2 (de) |
ZA (1) | ZA200405637B (de) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008540366A (ja) * | 2005-05-02 | 2008-11-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規結晶性臭化チオトロピウム |
JP2008540367A (ja) * | 2005-05-02 | 2008-11-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規結晶性臭化チオトロピウム |
Families Citing this family (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8815258B2 (en) | 2009-05-29 | 2014-08-26 | Pearl Therapeutics, Inc. | Compositions, methods and systems for respiratory delivery of two or more active agents |
AU2015201037C1 (en) * | 2009-05-29 | 2017-07-27 | Pearl Therapeutics, Inc. | Respiratory delivery of active agents |
SI3111927T1 (sl) * | 2009-05-29 | 2020-08-31 | Pearl Therapeutics, Inc. | Sestavki za respiratorni vnos aktivnih učinkovin in s tem povezani postopki in sistemi |
JP6454323B2 (ja) | 2013-03-15 | 2019-01-16 | パール セラピューティクス,インコーポレイテッド | 粒子状結晶性材料のコンディショニングのための方法及びシステム |
EP3922240B1 (de) * | 2016-09-19 | 2023-06-21 | Mexichem Fluor S.A. de C.V. | Pharmazeutische zusammensetzung enthaltend tiotropiumbromide |
Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0418716A1 (de) * | 1989-09-16 | 1991-03-27 | Boehringer Ingelheim Kg | Neue Thienylcarbonsäureester von Aminoalkoholen, ihre Quaternierungsprodukte sowie die Herstellung und Verwendung dieser Verbindungen |
WO2000007567A1 (de) * | 1998-08-04 | 2000-02-17 | Jago Research Ag | Medizinische aerosolformulierungen |
WO2001078741A1 (en) * | 2000-04-18 | 2001-10-25 | Glaxo Group Limited | Medical combinations comprising tiotropium and budesonide |
WO2001078743A1 (en) * | 2000-04-18 | 2001-10-25 | Glaxo Group Limited | Medical combinations comprising tiotropium and mometasone |
WO2001078736A1 (en) * | 2000-04-18 | 2001-10-25 | Glaxo Group Limited | Medical combinations comprising tiotropium and rofleponide |
WO2001078739A1 (en) * | 2000-04-18 | 2001-10-25 | Glaxo Group Limited | Medical combinations comprising tiotropium and fluticasone proprionate |
WO2002036163A2 (de) * | 2000-10-31 | 2002-05-10 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue arzneimittelkompositionen aus tiotropiumsalzen und antihistaminika zur therapie von atemwegserkrankungen |
WO2002069944A2 (de) * | 2001-03-08 | 2002-09-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue arzneimittelkompositionen auf der basis von anticholinergika und nk1-rezeptor-antagonisten |
WO2002074034A2 (de) * | 2001-03-20 | 2002-09-26 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue arzneimittelkompositionen auf der basis von anticholinergika und endothelinantagonisten |
-
2002
- 2002-03-28 DE DE10214264A patent/DE10214264A1/de not_active Withdrawn
-
2003
- 2003-03-20 NZ NZ536030A patent/NZ536030A/en not_active IP Right Cessation
- 2003-03-20 UA UA20041008758A patent/UA79776C2/uk unknown
- 2003-03-20 ME MEP-2008-473A patent/ME00246B/de unknown
- 2003-03-20 MX MXPA04009338A patent/MXPA04009338A/es active IP Right Grant
- 2003-03-20 RS YU86004A patent/RS52481B/en unknown
- 2003-03-20 IL IL16369603A patent/IL163696A0/xx unknown
- 2003-03-20 WO PCT/EP2003/002899 patent/WO2003082244A2/de active Application Filing
- 2003-03-20 JP JP2003579782A patent/JP5147158B2/ja not_active Expired - Lifetime
- 2003-03-20 EA EA200401159A patent/EA008610B1/ru unknown
- 2003-03-20 EP EP03717219A patent/EP1492498A2/de not_active Withdrawn
- 2003-03-20 BR BR0308709-3A patent/BR0308709A/pt active Pending
- 2003-03-20 AU AU2003221509A patent/AU2003221509B2/en not_active Expired
- 2003-03-20 PL PL03371295A patent/PL371295A1/xx not_active Application Discontinuation
- 2003-03-20 CN CNA038072475A patent/CN1642525A/zh active Pending
- 2003-03-20 CA CA2479638A patent/CA2479638C/en not_active Expired - Fee Related
- 2003-03-20 KR KR1020047015174A patent/KR101005717B1/ko active IP Right Grant
-
2004
- 2004-07-15 ZA ZA2004/05637A patent/ZA200405637B/en unknown
- 2004-09-23 NO NO20044004A patent/NO20044004L/no not_active Application Discontinuation
- 2004-09-27 HR HR20040890A patent/HRP20040890A2/hr not_active Application Discontinuation
- 2004-09-28 EC EC2004005322A patent/ECSP045322A/es unknown
Patent Citations (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0418716A1 (de) * | 1989-09-16 | 1991-03-27 | Boehringer Ingelheim Kg | Neue Thienylcarbonsäureester von Aminoalkoholen, ihre Quaternierungsprodukte sowie die Herstellung und Verwendung dieser Verbindungen |
WO2000007567A1 (de) * | 1998-08-04 | 2000-02-17 | Jago Research Ag | Medizinische aerosolformulierungen |
WO2001078741A1 (en) * | 2000-04-18 | 2001-10-25 | Glaxo Group Limited | Medical combinations comprising tiotropium and budesonide |
WO2001078743A1 (en) * | 2000-04-18 | 2001-10-25 | Glaxo Group Limited | Medical combinations comprising tiotropium and mometasone |
WO2001078736A1 (en) * | 2000-04-18 | 2001-10-25 | Glaxo Group Limited | Medical combinations comprising tiotropium and rofleponide |
WO2001078739A1 (en) * | 2000-04-18 | 2001-10-25 | Glaxo Group Limited | Medical combinations comprising tiotropium and fluticasone proprionate |
WO2002036163A2 (de) * | 2000-10-31 | 2002-05-10 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue arzneimittelkompositionen aus tiotropiumsalzen und antihistaminika zur therapie von atemwegserkrankungen |
WO2002069944A2 (de) * | 2001-03-08 | 2002-09-12 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue arzneimittelkompositionen auf der basis von anticholinergika und nk1-rezeptor-antagonisten |
WO2002074034A2 (de) * | 2001-03-20 | 2002-09-26 | Boehringer Ingelheim Pharma Gmbh & Co. Kg | Neue arzneimittelkompositionen auf der basis von anticholinergika und endothelinantagonisten |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2008540366A (ja) * | 2005-05-02 | 2008-11-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規結晶性臭化チオトロピウム |
JP2008540367A (ja) * | 2005-05-02 | 2008-11-20 | ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング | 新規結晶性臭化チオトロピウム |
Also Published As
Publication number | Publication date |
---|---|
CA2479638A1 (en) | 2003-10-09 |
WO2003082244A3 (de) | 2004-02-05 |
EP1492498A2 (de) | 2005-01-05 |
AU2003221509A1 (en) | 2003-10-13 |
JP5147158B2 (ja) | 2013-02-20 |
KR101005717B1 (ko) | 2011-01-05 |
YU86004A (sh) | 2006-08-17 |
NZ536030A (en) | 2006-07-28 |
AU2003221509B2 (en) | 2008-01-24 |
ECSP045322A (es) | 2005-01-28 |
EA008610B1 (ru) | 2007-06-29 |
EA200401159A1 (ru) | 2005-04-28 |
JP2005527550A (ja) | 2005-09-15 |
RS52481B (en) | 2013-02-28 |
HRP20040890A2 (en) | 2005-06-30 |
CN1642525A (zh) | 2005-07-20 |
ZA200405637B (en) | 2005-07-27 |
MXPA04009338A (es) | 2005-01-25 |
KR20040098022A (ko) | 2004-11-18 |
DE10214264A1 (de) | 2003-10-16 |
PL371295A1 (en) | 2005-06-13 |
BR0308709A (pt) | 2005-01-04 |
UA79776C2 (en) | 2007-07-25 |
IL163696A0 (en) | 2005-12-18 |
CA2479638C (en) | 2011-01-04 |
NO20044004L (no) | 2004-10-05 |
ME00246B (de) | 2011-05-10 |
MEP47308A (en) | 2011-02-10 |
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